Ossining Holidays from AU$2,912

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Your Ossining Holiday

With one of our holiday packages to Ossining, you'll find countless opportunities for fun and relaxation. There's tons to experience, including its rich history and spectacular views. Make your trip to Ossining even more fun by going sightseeing. Van Cortlandt Manor, Sleepy Hollow Cemetery and Tarrytown Music Hall are among the popular attractions worth exploring. Don't delay your visit to this city any longer. Your ultimate Ossining holiday is only a few clicks away with Expedia.

The Latest Ossining Holiday Deals

Price found within the past 48 hours. Click for updated prices.
Hotel St. James

Hotel St. James

3 out of 5
Manhattan
Price was AU$4,169, price is now AU$2,912 per person
AU$2,912
per person
28 Sept - 5 Oct
found 1 day ago
Return flight included
Sydney (SYD) to New York (JFK)
8.8/10 Excellent! (7,519 reviews)
Great location!

Reviewed on 13 July 2026

Margaritaville Resort Times Square

Margaritaville Resort Times Square

4 out of 5
Manhattan
Price was AU$4,335, price is now AU$3,199 per person
AU$3,199
per person
28 Sept - 5 Oct
found 1 day ago
Return flight included
Sydney (SYD) to New York (JFK)
9/10 Wonderful! (4,331 reviews)
Very clean, updates property. Comfortable rooms.

Reviewed on 12 July 2026

Candlewood Suites New York City-Times Square by IHG

Candlewood Suites New York City-Times Square by IHG

2.5 out of 5
Manhattan
Price was AU$3,992, price is now AU$2,987 per person
AU$2,987
per person
28 Sept - 5 Oct
found 1 day ago
Return flight included
Sydney (SYD) to New York (JFK)
8.6/10 Excellent! (2,026 reviews)
Just a little worn....but otherwise great and good location. Staff was attentive.

Reviewed on 12 July 2026

The Lombardy Hotel

The Lombardy Hotel

4 out of 5
Manhattan
Price was AU$4,907, price is now AU$3,678 per person
AU$3,678
per person
28 Sept - 5 Oct
found 6 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
9/10 Wonderful! (1,530 reviews)
Location is great. It is close to metro stations and 5th Ave. we booked the double queen bed suites which are very spacious. while the restrooms are small and not clean.

Reviewed on 12 July 2026

OYO Times Square

OYO Times Square

4 out of 5
Manhattan
Price was AU$4,094, price is now AU$3,108 per person
AU$3,108
per person
28 Sept - 5 Oct
found 6 hours ago
Return direct flight included
Sydney (SYD) to New York (JFK)
6.8/10 (1,983 reviews)
Easily the worst property we have ever stayed in. Small room, not clean well, the nosies bed we ever slept on...a/c was loud and it didn't conceal the noise from bed! Honestly cannot recommend this hotel at any price! Let alone NYC prices.

Reviewed on 12 July 2026

Ossining Holiday

Ossining Essential Information

Language
English
Currency
U.S dollars
Closest Airport
LaGuardia Airport (LGA)
Population
25,400
Max Temp Winter
2ºC
Max Temp Summer
27ºC
Top Sights
Bear Mountain State Park, Franklin D. Roosevelt State Park and Paramount Hudson Valley Theatre

Our pick of the best Ossining Hotel Deals

Windrose On Hudson

Windrose On Hudson

3 out of 5
1 Shady Lane Farm Road Ossining NY
The price is AU$330 per night from 19 July to 20 July
AU$330
19 July - 20 July
includes taxes & fees
8.6/10 Excellent! (188 reviews)
"Beautiful location and good property for YOUNG, ATHLETIC folks able to navigate the hills and distances between venues. Not so good for those with disabilities or just tired old knees, hips and hearts! Doors very heavy and w/o automated openers, shower floors very slippery, only two USB outlets in ..."

Reviewed on 8 July 2026

Windrose On Hudson
Armoni Inn & Suites

Armoni Inn & Suites

3.5 out of 5
329 Route 303 Orangeburg NY
Fully refundableReserve now, pay when you stay
The price is AU$138 per night from 14 July to 15 July
AU$138
14 July - 15 July
includes taxes & fees
6/10 (2,295 reviews)
"This was a very disappointing stay, to which we will never return again. None of the amenities that were advertised were available to us as guests (pool, gym, lounge, continental breakfast). When entering the room, there were no towels, hangers, soap, etc. (BASIC amenities that should be provided). ..."

Reviewed on 12 July 2026

Armoni Inn & Suites
Sonesta White Plains Downtown

Sonesta White Plains Downtown

4 out of 5
66 Hale Ave White Plains NY
Fully refundableReserve now, pay when you stay
The price is AU$352 per night from 13 Aug to 14 Aug
AU$352
13 Aug - 14 Aug
includes taxes & fees
8.8/10 Excellent! (1,330 reviews)
"Staff at the dining area are sweet and nice. The younger white man who booked my room, helped me to get Uber to the convention hall was fine. Two middle aged Latina women, ( day time) are unhelpful, stupid, and unfriendly. They also don't understand English. Should be replaced or moved to other jobs. ..."

Reviewed on 11 July 2026

Sonesta White Plains Downtown
See all 1,327 properties in Ossining
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
All Inclusive Holidays
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Stay near popular Ossining attractions

A dam with a reservoir, surrounded by autumn foliage and hills.

Travelers Rest

This historic former stagecoach stop serves exceptional American and German cuisine in elegant, fireplace-lit dining rooms. Stroll through the landscaped gardens with waterfalls before your memorable meal.
See properties

Frequently asked questions

How much does an Ossining holiday package cost?
You can snap up a holiday package to this popular destination from AU$2,912 on Expedia. However, how much your holiday to Ossining costs will depend on the season, hotel choice and length of stay.
What are the cheapest months to go to Ossining?
The off-season is the best time to head to Ossining if you're hoping to keep costs down. Another tip for scoring cheap Ossining holiday packages? Try to avoid visiting during public holidays and any major festivals.
How many days is enough for Ossining?
To fully enjoy your Ossining holiday, we recommend staying for 5 days. Divide your time between visiting Teatown Lake Reservation, Kitchawan Preserve and other top attractions, in addition to experiencing neighbourhoods like Town of Mount Pleasant and Pleasantville. If you've got some time to spare, add a tour or day trip to your Ossining holiday itinerary.
Is it worth booking a holiday package to Ossining?
Ossining has everything you need for an unforgettable escape. Get your Ossining holiday off to a flying start by visiting top attractions like Louis Engel Waterfront Park.
How to find the best Ossining package deals?
Use Expedia's handy filters to find some tempting Ossining package deals. When you start your search, just set your maximum budget and then sort the results by "Price: low to high." If you want to save, plan your adventure for midweek, or look for Ossining package deals in the off-season. Play around with your travel dates and you may score even bigger discounts. As a rule of thumb, it's usually best to book your holiday package well in advance.
Is it cheaper to book an Ossining holiday as a package?
You can enjoy significant savings on your Ossining retreat by booking a personalised holiday package. Click on the "Package" heading, then select your travel dates and destination to view some great hotel and flight prices. Bundle everything into a neat package and you can save hundreds of dollars. Consider adding a car rental and you may land a better deal.
When to book a holiday package to Ossining?
If you have your Ossining travel dates locked in, book as early as you can to grab some incredible deals. With Expedia, you can often reserve some flights up to one year in advance. Prefer spur-of-the-moment adventures? Our last-minute deals are great for impromptu escapes.
How to plan a trip to Ossining?

  1. Pick the best time to travel: Your schedule, preferred season and the type of weather you like can all impact your decision on when to travel to Ossining.
  2. Budget wisely: Besides the price of your accommodation, you'll need to consider other expenses too. These include transportation, food and flights. Also, set aside some extra funds for unexpected expenses that may arise during your trip to Ossining.
  3. Set the duration of your trip: Start by listing all the attractions and activities you'd like to get to in Ossining. Then, estimate how long you'll need at each, including any travel time.
  4. Bundle your accommodation and airfare: After you've settled on your dates and duration, lock in the ideal Ossining holiday package for you.

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* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.